CA1296022C - Preparation de chlorhydrates d'hydroxylamine o-substitues - Google Patents

Preparation de chlorhydrates d'hydroxylamine o-substitues

Info

Publication number: CA1296022C
Authority: CA; Canada
Prior art keywords: hydrogen chloride; preparation; acetoxime; substituted hydroxylamine; ether
Prior art date: 1986-09-12
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA000546726A

Other languages

English (en)

Inventor

Wolfgang Will

Tillmann Faust

Peter Schaefer

Horst Hartmann

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-09-12

Filing date

1987-09-11

Publication date

1992-02-18

1987-09-11 Application filed by BASF SE filed Critical BASF SE

1992-02-18 Application granted granted Critical

1992-02-18 Publication of CA1296022C publication Critical patent/CA1296022C/fr

2009-02-18 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims description 9
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical class Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 title description 5
-1 O-substituted hydroxylamine hydrochlorides Chemical class 0.000 claims abstract description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 18
229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 14
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
230000007062 hydrolysis Effects 0.000 claims abstract 2
238000006460 hydrolysis reaction Methods 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 10
PDQYOPNIPOWAFS-ARJAWSKDSA-N (2z)-2-hydroxyiminopropanal Chemical compound O=CC(/C)=N\O PDQYOPNIPOWAFS-ARJAWSKDSA-N 0.000 claims description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
238000003776 cleavage reaction Methods 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
239000007789 gas Substances 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 5
PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
230000000875 corresponding effect Effects 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 3
150000002443 hydroxylamines Chemical class 0.000 description 3
239000000243 solution Substances 0.000 description 3
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000011814 protection agent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
FXCXOKOKILDXCL-GGWOSOGESA-N (e)-1-[(e)-but-2-enoxy]but-2-ene Chemical compound C\C=C\COC\C=C\C FXCXOKOKILDXCL-GGWOSOGESA-N 0.000 description 1
LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001145 hydrido group Chemical class *[H] 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
OPJFWQSEOAELRV-SQQVDAMQSA-N o-[(e)-but-2-enyl]hydroxylamine;hydrochloride Chemical compound Cl.C\C=C\CON OPJFWQSEOAELRV-SQQVDAMQSA-N 0.000 description 1
NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000010409 thin film Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/20—Hydroxylamino compounds or their ethers or esters having oxygen atoms of hydroxylamino groups etherified

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000546726A 1986-09-12 1987-09-11 Preparation de chlorhydrates d'hydroxylamine o-substitues Expired - Lifetime CA1296022C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP3631071.9		1986-09-12
DE19863631071 DE3631071A1 (de)	1986-09-12	1986-09-12	Verfahren zur herstellung von o-substituierten hydroxylamin-hydrochloriden

Publications (1)

Publication Number	Publication Date
CA1296022C true CA1296022C (fr)	1992-02-18

Family

ID=6309445

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000546726A Expired - Lifetime CA1296022C (fr)	1986-09-12	1987-09-11	Preparation de chlorhydrates d'hydroxylamine o-substitues

Country Status (5)

Country	Link
EP (1)	EP0259850B1 (fr)
JP (1)	JPH07108890B2 (fr)
AT (1)	ATE65244T1 (fr)
CA (1)	CA1296022C (fr)
DE (2)	DE3631071A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103113257A (zh) *	2013-03-08	2013-05-22	福州大学	合成甲氧胺盐酸盐的连续反应精馏设备及其工艺

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4233333A1 (de) *	1992-10-05	1994-04-07	Basf Ag	Verfahren zur Herstellung von O-substituierten Hydroxylammoniumsalzen
US5393921A (en) *	1993-07-07	1995-02-28	The Gillette Company	Process for synthesizing O-substituted oxime compounds and conversion to the corresponding O-substituted hydroxylamine
CA2168457A1 (fr) *	1993-07-31	1995-02-09	Ulrich Klein	Methode de preparation de derives de substitution en o de sels d'hydroxylammonium
US5488162A (en) *	1994-01-03	1996-01-30	Buckland; Paul R.	Process for preparing o-alkylhydroxylamine salts without the isolation of intermediates
US5777164A (en) *	1997-04-14	1998-07-07	Eastman Chemical Company	Process for the preparation of high purity O-substituted hydroxylamine derivatives
DE19911234A1 (de) *	1999-03-15	2000-09-28	Basf Ag	Verfahren zur kontinuierlichen Herstellung von Methoxyamin-Hydrochlorid
JP2002039836A (ja) *	2000-07-21	2002-02-06	Nippon Soda Co Ltd	連続抽出における中間層の液面制御方法
US7214825B2 (en)	2003-10-17	2007-05-08	Honeywell International Inc.	O-(3-chloropropenyl) hydroxylamine free base
CN110606813A (zh) *	2019-09-17	2019-12-24	浙江圣安化工股份有限公司	一种含活性基团的肟醚及其合成方法
CN113636953B (zh) *	2021-08-16	2024-04-19	诚弘制药(威海)有限责任公司	一种o-/n-烷基取代羟胺盐的制备方法

1986
- 1986-09-12 DE DE19863631071 patent/DE3631071A1/de not_active Withdrawn
1987
- 1987-09-09 DE DE8787113161T patent/DE3771423D1/de not_active Expired - Lifetime
- 1987-09-09 JP JP62224217A patent/JPH07108890B2/ja not_active Expired - Lifetime
- 1987-09-09 EP EP87113161A patent/EP0259850B1/fr not_active Expired - Lifetime
- 1987-09-09 AT AT87113161T patent/ATE65244T1/de not_active IP Right Cessation
- 1987-09-11 CA CA000546726A patent/CA1296022C/fr not_active Expired - Lifetime

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103113257A (zh) *	2013-03-08	2013-05-22	福州大学	合成甲氧胺盐酸盐的连续反应精馏设备及其工艺
CN103113257B (zh) *	2013-03-08	2015-04-15	福州大学	合成甲氧胺盐酸盐的连续反应精馏设备及其工艺

Also Published As

Publication number	Publication date
JPS63152350A (ja)	1988-06-24
EP0259850A2 (fr)	1988-03-16
JPH07108890B2 (ja)	1995-11-22
DE3631071A1 (de)	1988-03-24
EP0259850B1 (fr)	1991-07-17
EP0259850A3 (en)	1988-09-28
DE3771423D1 (de)	1991-08-22
ATE65244T1 (de)	1991-08-15

Legal Events

Date	Code	Title	Description
2009-02-18	MKLA	Lapsed
2012-12-05	MKEC	Expiry (correction)	Effective date: 20121205

Publication	Publication Date	Title
US4439616A (en)	1984-03-27	Tertiary aralkyl urethanes and isocyanates derived therefrom
CA1296022C (fr)	1992-02-18	Preparation de chlorhydrates d'hydroxylamine o-substitues
EP0103400B1 (fr)	1986-05-14	Procédé pour la préparation de carbohydrazide
EP0158159B1 (fr)	1988-10-05	Procédé pour la synthèse d'oximes-o-substituées et leur conversion en hydroxylamines o-substituées correspondantes
US4981996A (en)	1991-01-01	Method for the production of O-substituted hydroxylamines
US3850924A (en)	1974-11-26	Process for preparing herbicidal triazines
US4681946A (en)	1987-07-21	Preparation of nicotinamide
CN113227058B (zh)	2025-06-24	用于制备4,6-二羟基嘧啶的改进方法
US6696590B2 (en)	2004-02-24	Process for the synthesis of aliphatic, cycloaliphatic or araliphatic chloroformates
US6087499A (en)	2000-07-11	Process for producing 5-perfluoroalkyluracil derivatives
JP4833419B2 (ja)	2011-12-07	環式酸の製造
US3057919A (en)	1962-10-09	N-(salicyl)-benzamide derivatives
JP2743461B2 (ja)	1998-04-22	１―メチル―３―アルキル―５―ピラゾールカルボン酸エステル類の製造法
US4095034A (en)	1978-06-13	Manufacture of α-naphthyl-N-methyl-carbamate
US2762841A (en)	1956-09-11	Process of producing l-glutamine
US3787470A (en)	1974-01-22	Preparation of thiolhydroxamate esters from nitroalkanes
CA1063612A (fr)	1979-10-02	Procede pour la production de derives du 3-hydroxy-1,2,4,-triazole
JPS5941984B2 (ja)	1984-10-11	クロロチオ−ル蟻酸エステルの製造方法
US4770820A (en)	1988-09-13	Process for the preparation of carbamoyl chlorides derived from secondary amines
WO1987005600A1 (fr)	1987-09-24	Procede de preparation d'isocyanate de methyle
EP0534347B1 (fr)	1995-06-28	Procédé de préparation de N-éthylhydroxylamine-hydrochloride
CA2072735A1 (fr)	1993-02-14	Procede pour la preparation d'halogenure de succinylcholine
EP1321455B1 (fr)	2005-02-02	Procédé pour la préparation du (3-trifluorométhylphényl)-1-(2-(benzoyloxy)éthylamino)-2-propane
US5705666A (en)	1998-01-06	Process for the preparation of crystalline O-isopropylisourea hydrochloride
EP0103919A2 (fr)	1984-03-28	Procédé de préparation d'urées substituées asymétriques